IBMX

{{Technical|date=May 2023}}

{{chembox

| Watchedfields = changed

| verifiedrevid = 443866049

| ImageFileL1 = IBMX structure.svg

| ImageSizeL1 = 120

| ImageAltL1 = Skeletal formula of IBMX

| ImageFileR1 = IBMX 3D spacefill.png

| ImageSizeR1 = 130

| ImageAltR1 = Space-filling model of the IBMX model

| IUPACName = 1-Methyl-3-(2-methylpropyl)-7H-purine-2,6-dione

| OtherNames = 3-Isobutyl-1-methylxanthine

| Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 3627

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C13708

| InChI = 1/C10H14N4O2/c1-6(2)4-14-8-7(11-5-12-8)9(15)13(3)10(14)16/h5-6H,4H2,1-3H3,(H,11,12)

| InChIKey = APIXJSLKIYYUKG-UHFFFAOYAL

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 275084

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C10H14N4O2/c1-6(2)4-14-8-7(11-5-12-8)9(15)13(3)10(14)16/h5-6H,4H2,1-3H3,(H,11,12)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = APIXJSLKIYYUKG-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 28822-58-4

| PubChem = 3758

| IUPHAR_ligand = 388

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB07954

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = TBT296U68M

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 34795

| SMILES = CC(C)Cn1c2c(c(=O)n(c1=O)C)[nH]cn2

}}

| Section2 = {{Chembox Properties

| Formula = C₁₀H₁₄N₄O₂

| MolarMass = 222.3 g/mol

| Appearance = White solid

| Density =

| MeltingPtC = 199 to 201

| MeltingPt_notes =

| BoilingPt =

| Solubility =

| SolubleOther = Soluble in ethanol, DMSO, and methanol

}}

| Section3 = {{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

IBMX (3-isobutyl-1-methylxanthine), like other methylxanthine derivatives, is both a:

1. competitive non-selective phosphodiesterase inhibitor{{cite journal | last1 = Essayan | first1 = DM | title = Cyclic Nucleotide Phosphodiesterases | journal = The Journal of Allergy and Clinical Immunology | date = November 2001 | volume = 108 | issue = 5 | pages = 671–80 | doi = 10.1067/mai.2001.119555 | pmid = 11692087| doi-access = free }} which raises intracellular cAMP, activates PKA, inhibits TNFα{{cite journal | last1 = Deree | first1 = J | last2 = Martins | first2 = JO | last3 = Melbostad | first3 = H | last4 = Loomis | first4 = WH | last5 = Coimbra | first5 = R | title = Insights into the Regulation of TNF-α Production in Human Mononuclear Cells: The Effects of Non-Specific Phosphodiesterase Inhibition | journal = Clinics (Sao Paulo) | date = June 2008 | volume = 63 | issue = 3 | pages = 321–8 | doi = 10.1590/S1807-59322008000300006 | pmid = 18568240 | pmc = 2664230}}{{cite journal | last1 = Marques | first1 = LJ | last2 = Zheng | first2 = L | last3 = Poulakis | first3 = N | last4 = Guzman | first4 = J | last5 = Costabel | first5 = U | title = Pentoxifylline Inhibits TNF-α Production from Human Alveolar Macrophages | journal = American Journal of Respiratory and Critical Care Medicine | date = February 1999 | volume = 159 | issue = 2 | pages = 508–11 | doi = 10.1164/ajrccm.159.2.9804085 | pmid = 9927365 | url = http://www.atsjournals.org/doi/full/10.1164/ajrccm.159.2.9804085#readcube-epdf| url-access = subscription }} and leukotriene{{cite journal | last1 = Peters-Golden | first1 = M | last2 = Canetti | first2 = C | last3 = Mancuso | first3 = P | last4 = Coffey | first4 = MJ | title = Leukotrienes: Underappreciated Mediators of Innate Immune Responses | journal = Journal of Immunology | date = 15 January 2005 | volume = 174 | issue = 2 | pages = 589–94 | doi = 10.4049/jimmunol.174.2.589 | pmid = 15634873 | url = http://www.jimmunol.org/content/174/2/589.full.pdf| doi-access = free }} synthesis, and reduces inflammation and innate immunity, and
2. nonselective adenosine receptor antagonist.{{cite journal | last1 = Daly | first1 = JW | last2 = Jacobson | first2 = KA | last3 = Ukena | first3 = D | title = Adenosine Receptors: Development of Selective Agonists and Antagonists | journal = Progress in Clinical and Biological Research | date = 1987 | volume = 230 | pages = 41–63 | pmid = 3588607}}

As a phosphodiesterase inhibitor, IBMX has IC₅₀ = 2–50 μM{{cite journal | last1 = Beavo | first1 = JA | last2 = Rogers | first2 = NL | last3 = Crofford | first3 = OB | last4 = Hardman | first4 = JG | last5 = Sutherland | first5 = EW | last6 = Newman | first6 = EV | title = Effects of Xanthine Derivatives on Lipolysis and on Adenosine 3',5'-Monophosphate Phosphodiesterase Activity | journal = Molecular Pharmacology | date = November 1970 | volume = 6 | issue = 6 | pages = 597–603 | pmid = 4322367}} and does not inhibit PDE8 or PDE9.{{cite journal | last1 = Soderling | first1 = SH | last2 = Beavo | first2 = JA | title = Regulation of cAMP and cGMP Signaling: New Phosphodiesterases and New Functions | journal = Current Opinion in Cell Biology | date = April 2000 | volume = 12 | issue = 2 | pages = 174–9 | pmid = 10712916 | doi=10.1016/s0955-0674(99)00073-3}}